It's not a bad strategy, especially if you live in a lower-priced area with a good rent-to-purchase price ratio.

We do this for a living and our reputation depends on you successfully securing a loan, on time, and as promised. 

If there's a hole, it may be a red flag.b) sensitivity analysis: I examine all the assumptions, and make sure I can live with the worst case scenarios.c) "Stall and see": if they are getting money over multiple years, and there is no penalty for investing later, I would usually wait so I get some real performance data, versus having to look at theoretical pro forma information.d) Recession stress test: I will not invest in anything, until I subject it to recession level stress and see if I can live with the result.

I specialize in working with Canadians that own property down here (I live in Palm Springs, we might be the snowbird capital of the world?).

No, not places you heard people want to live, or were told, or think, no-no-no, where you KNOW people want to live. 

They just live T get you to apply and paper appraisals.

He wants to live in one and use the other for his studio. 

Quote from @Scott Mac: Safety - Inherit a fully paid for SFH, in decent condition, in the neighborhood you live in, and rent it out to long term tenants who you are comfortable with.

Starting to research Uruguay to invest and as a 3rd country to live in.  

I live in Tampa Florida.